Best time to repot is Spring. Always plan to repot most orchids at that time before new roots get longer than an inch. The danger of repotting now is damage to roots and new growths which depend on those roots.

If you have roots hanging out of the pot, just stick the whole plant with pot inside a larger pot to get it through winter. The larger pot will provide humidity around those roots so they don't dry out.

That's what I always did and orchids love it. You can put a few pieces of Styrofoam pieces or chunks of bark to keep the pot from moving around inside the bigger pot.

In this picture, you can see two Cattleyas growing happily sitting inside larger pots/baskets. The yellow one is actually in its third pot-in-pot. The orginal pot was a small plastic pot which is sitting inside a bigger clay pot which is now sitting inside an even bigger clay pot! I call it, 'lazy gardening.'

Orchids seem to do fine with it.

Thanks Jane-I can certainly do that-I'll plan on it. I suppose the growth being crowded isn't going to hurt anything, I was mostly concerned about the roots drying out during the winter. This makes perfectly good sense, thanks again!